Benzene → 4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]cinnamaldehyde

HRID 977241Notes

Reaction equation

HRID 977241 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:24]=[CH:23][C:20](C=O)=[CH:19][CH:18]=1)=[O:16].C1(P(=[CH:44][CH:45]=[O:46])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:47]1C=CC=CC=1>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:47]=[CH:44][CH:45]=[O:46])=[CH:19][CH:18]=1)=[O:16]

Participants

4

Reactant 3

HCID 241BenzeneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 144566554-[3-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]benzaldehyde

Product 1

HCID 545392864-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]cinnamaldehydeYield 63%

Procedure

A mixture of 4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]benzaldehyde (6.0 g), (triphenylphosphoranylidene)acetaldehyde [(C6H5)3P=CHCHO](6.29 g) and benzene (100 ml) was stirred under refluxing conditions for 24 hours. The reaction mixture was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:2), 4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]cinnamaldehyde (4.08 g, 63%) was obtained, which was then recrystallized from dichloromethane-isopropyl ether to yield colorless prisms having a melting point of 119°-120° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washFrom the fraction eluted with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-e8cf2b1f4d4942a1a9460423b6efecb2
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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